Abstract
The tert-butyl ester of 3-methoxy-2-pyrrolecarboxylic acid 3 undergoes reaction with singlet oxygen to form an intermediate imino hydroperoxide 4. This hydroperoxide may be trapped by a variety of nucleophiles yielding 5-substituted pyrroles 6. With strong nucleophilic substituents at the 5-position, these pyrroles may add to unreacted hydroperoxide 4 to form bipyrrole-like products 7.
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